Retene

Chemical compound From Wikipedia, the free encyclopedia

Retene

Retene, methyl isopropyl phenanthrene or 1-methyl-7-isopropyl phenanthrene, C18H18, is a polycyclic aromatic hydrocarbon present in the coal tar fraction, boiling above 360 °C. It occurs naturally in the tars obtained by the distillation of resinous woods. It crystallizes in large plates, which melt at 98.5 °C and boil at 390 °C. It is readily soluble in warm ether and in hot glacial acetic acid. Sodium and boiling amyl alcohol reduce it to a tetrahydroretene, but if it heated with phosphorus and hydriodic acid to 260 °C, a dodecahydride is formed. Chromic acid oxidizes it to retene quinone, phthalic acid and acetic acid. It forms a picrate that melts at 123-124 °C.

Quick Facts Names, Identifiers ...
Retene
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Skeletal formula
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Ball-and-stick model
Names
Preferred IUPAC name
1-Methyl-7-(propan-2-yl)phenanthrene
Other names
Retene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.908
EC Number
  • 207-597-9
UNII
  • InChI=1S/C18H18/c1-12(2)14-7-10-17-15(11-14)8-9-16-13(3)5-4-6-18(16)17/h4-12H,1-3H3 N
    Key: NXLOLUFNDSBYTP-UHFFFAOYSA-N N
  • InChI=1/C18H18/c1-12(2)14-7-10-17-15(11-14)8-9-16-13(3)5-4-6-18(16)17/h4-12H,1-3H3
    Key: NXLOLUFNDSBYTP-UHFFFAOYAL
  • Cc1cccc3c1ccc2cc(C(C)C)ccc23
Properties
C18H18
Molar mass 234.33552
Melting point 98.5 °C (209.3 °F; 371.6 K)
Boiling point 390 °C (734 °F; 663 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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Retene is derived by degradation of specific diterpenoids biologically produced by conifer trees. The presence of traces of retene in the air is an indicator of forest fires; it is a major product of pyrolysis of conifer trees.[1][failed verification see discussion] It is also present in effluents from wood pulp and paper mills.[2]

Retene, together with cadalene, simonellite and ip-iHMN, is a biomarker of vascular plants, which makes it useful for paleobotanic analysis of rock sediments. The ratio of retene/cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere.[3]

Health effects

A recent study has shown retene, which is a component of the Amazonian organic PM10, is cytotoxic to human lung cells.[4]

References

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